Polyvinyl acetal resin compositions



Patented 14, 1948 lPGL ACETAL RESIN COMPOSITIONS Richard H. Hunt,Springfield, Mass, assignor to Monsanto Qheinical Company, St. Louis,Mo., a corporation of Delaware No Drawing. Application September s,1945,

Serial No. 614,811

12 Claims. (ill. sec-sac) i This invention relates to plasticizers forpoly s ived to p o e sh of elasti i d po y y vinyl acetal resins. Moreparticularly the lnven formal resin. tion relates to polyvinyl acetalresins plasticized Example V with terphenyls. 1 Parts an object of thisinvention is to provide a & Polyvinyl butyral resin loo new class ofplasticizers for polyvinyl acetal Meta diphenyl benzene resins.

A further object is to provide polyvinyl acetal The resin andplasticizer were cflmpolmded as resins pgasgicized t t 1 in Example I.The resultant sheets were more These and other bjects are attained bythe i0 flexible than unplasticized resin, but stifier than incorporationof'terphenyls into polyvinyl acetal the Sheets e according to Examp eThe resin. moisture resistance of the sheets was substantial- Thefollowing examples are given by way of ly improved compared to that ofthe unplasticized illustration and are not intended to limit theresinscope of this invention. Where parts are men- 15 The resin andplaslLicizer may be mixed hot tioned, they are parts by i ht malaxatlngrolls, or in a. Banbury mixer as shown in the examples or by any otherconventional Example I means for obtaining a homogeneous mass. They mayalso be mixed with the addition of a volatile solvent such as alcohol,acetone, ethyl acetate, etc., which is subsequently removed prior to orThe plasticizer was mined into the resin on after the formation of thedesired article. hot malaxating rolls until a homogeneous com- Inaddition to the and meta diphenyl position was obtained. The hot masswas then benzenes third isomer Paradiphenyl calendered into thin sheetswhich were more flex- Zene mlxture of two or an of the ismners PartsPolyvinyl butyral resin 100 20 Meta diphenyl benzene 2Q i-ble and morewater-resistant than similar sheets m be used- This is of particularadvantage f unplasticized resin since a mixture of the isomers isobtained in the commercial production of diphenyl benzene. Example IIThe polyvinyl acctal resins employed accord- Parts ing to this inventionmay be made by reacting Polyvinyl butyral resin 100 an aldehylde with apartially or completely hydroe Ortho diphenyl benzene lyzed polyvinylester. U. S. patent to Morrison et al., Reissue 20,430, dated June 29,1937, illustrates suitable methods for preparing such resins. Polyvinylacetal resins prepared in this manner may have a certain number of estergroups,

The resin and plasticizer were compounded as in Example I to obtain aflexible sheet of plasticized polyvinyl butyral resin.

Eagample 11 originally present in the polyvinyl ester, which Parts havenot been removed, as well as a certain Polyvinyl butyral resin 100number of hydroxyl groups (which have replaced Ortho diphenyl benzene 20ester groups) and havenot been replaced with Dlbutyl sebacate 37 1 Metalgroupsa Polyvinyl acetal resins may be made from va- The Tesm andplasticizers were mixed in rlous aldehydes or mixtures thereof, or evenfrom standard Banbury type mixer to produce a homoketones eontainmg anactive carbonyl group. or geneous mass. The mass was then extruded intofrom t s of aldehyde and t Thus, a ft. pliable web. formaldehyde,acetaldehyde, propionaldehyde,

- Emample 1V butyraldehyde,valeraldehyde,hexaldehyde,benz- Partsaldehyde, crotonaldehyde, cyclohexanone and Polyvinyl formal resin 1 50the like and mixtures thereof may be employed.

Polyvinyl acetal resins made from saturated Meta dipheny benzene loweraliphatic aldehydes are more commonly The resin and plasticizer weremixed in aused. In particular, polyvinyl acetal resins standard Banburymixer to produce a homomade with saturated aliphatic aldehydescongeneous mass. The mass was baked in a chase taining less than 6carbon atoms and especially under heat and pressure and the resultantcake those made with formaldehyde, acetaldehyde and some 3 butyraidehydeand mixtures thereof, are readily available.

According to one embodiment oi the present invention, the polyvinlyacetal resins employed may be considered to be made up, on a weightbasis, or 525% hydroxyl groups, calculated as polyvinyl alcohol, 040%acetate-groups, calculated as polyvinyl acetate, and the balance sub- Istantially acetal.

when the acetal is butyraldehyde acetal, ac-

1 cording to one embodiment of this invention, the polyvinyl acetalresin contains, on a weight basis,

16-20% lrvdroxyl groups, calculated as polyvinyl alcohol, and 040%acetate groups. calculated as polyvinyl acetate, and the balancesubstantiall butyraldehyde acetal.

when the acetal is formaldehyde acetal, ac-

cording to another embodiment of this invention, v

tains 13% hydroxyl groups calculated as poly vinyl alcohol, 2-6% acetategroups, calculated as polyvinyl acetateand the balance acetaldehyde andbutyraldehyde acetal groups, in a molar ratio of 65-50% acetaldehyde and-50% butyraldehyde acetal groups. 1 Y

- The plasticizers of this invention may be used alone or in conjunctionwith other known plasticizers for polyvinyl acetal resins such as alkyl,aralkyl or aryl esters of organic acids, trialkyl, or triarylphosphates, ether esters, such as alkoxy alkyl phthalates, etc.

Other conventional modifying agents may be added to the compositions ofthis invention, such as dyes, pigments, fillers, lubricants, natural ora synthetic resins, cellulose derivatives, etc.

The polyvinyl acetal resins plasticized with terphenyls may be used toproduce sheets, continuous webs, rods or tubes having varying degrees01' hardness depending on the amount of plasticizer present. It hasbeen'found that as little as 1 part of the plasticizer per 100 parts ofresin will substantially soften the polyvinyl ac'etal resins, while asmuch as parts of the plasticizer may be incorporated in 100 parts ofresin without sweating out of the plasticizer during storage.

The compositions oi this invention may be used in innumerableapplications, from watch crystals. playing cards and soundrecordingdiscs which require relatively hard, moisture-impervious mate'- rials,to safety glass plastics which require soft materials which retain theirstrength and toughness at the extremes of atmospherictemperatures.

The foregoing description is intended to be illustrative and notlimitative or this invention as set forth in the appended claims.

What is claimed is:

1. A polyvinyl acetal resin plasticized with from 1 to 50 parts of aterphenyl per parts of resin.

2. A polyvinyl butyral resin plasticized with from 1 to '50 parts of aterphenyl per 100 parts 0! resin.

3. A polyvinyl i'ormal' resin plastioized with from 1 to 50 parts or aterphenyl per 100 parts of resin.

4. A polyvinyl acetal resin plasticised with from 1 to 50 parts of amixture of isomeric terphenyls per 100 parts of resin.

5. A polyvinyl butyral resin plasticlzed with from 1 to 50 parts of amixture of isomeric terphenyls per 100 parts of resin.

6. A polyvinyl formal resin plasticized with from 1 to 50 parts of amixture or isomeric terphenyls per 100 parts of resin.

7. A polyvinyl acetal resin plasticized with from 1 to 50 parts of orthodiphenyl benzene per 100 12m polyvinyl formal resin plasticized withfrom 1 to 50 parts oi meta diphenylbenzene per 100 parts of resin.

RICHARD H. HUNT.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Name Date Moose Aug. 21, 1945 Number

